Abstract
The dependence of 1 J CH on the dielectric constant (ϵ) of the solvent has been studied in isopropylamine and isopropanol both by actual measurement and by calculation using the INDO-FPT-Solvaton method. In isopropylamine 1 J CH decreases with increasing ϵ, while in isopropanol it increases with ϵ, trends which are reproduced by the calculations. This difference is believed to relate to the fact that the calculated excitation energy increases with ϵ in the former compound but decreases as ϵ increases in the latter. Regarding the effects of internal rotation, it is deduced that a trans orientation of the lone pair on the nitrogen or oxygen atom relative to the CH bond in the isopropyl group, draws p electron density towards the CH bond, thus reducing the s character of the bond and consequently yielding smaller 1 J CH values.
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